Making Sure She Has A Good Time, No Matter What

So now I’ve been on the ill-fated third date that preoccupied my thoughts all winter break. I initially had a somewhat doomed attitude about the idea of the third date, stemming from the fact that I basically stewed in my doubts about whether this was going to work or not for over a week in between dates. This was a violation Shidduch Rule #6 – never let over a week go by between dates, especially early on, unless there are unavoidable conflicts – it just isn’t good for the developing relationship. However, having spent a very nice, relaxing Shabbos with my distant relatives put me in a very positive mood, which helped me refocuse my mindset and allowed me to wholeheartedly go into the date without any expectations one way or the other – even half-hoping that my mental gymnastics had been entirely for naught and that things could turn out for the better.

Parenthetically, that #6 was entirely arbitrary, just for the record. I don’t have any formal set of “rules” that I abide by, in case you’re wondering. Any regulations that I do believe in are mostly common sense points like this notion regarding timing.

Unfortunately (or is that fortunately?), the issues that had planted the seeds of doubt in my mind were still very apparent, so I decided to end things here. She is really a lovely person who is very steeped in chesed and maintains close ties to her loving family (who are also very big chesed people). Not to mention the fact that she is rather attractive… The key issue was the intellectual thing I mentioned a few posts back. I don’t think it serves as a detriment to her personally, especially since she is a very serious student, but that component was entirely lacking in our conversation, which left me feeling very disconnected. I tried several times to bring up ideas that I figured would arouse interest that could lead to a deeper discussion, but she never took my lead, nor began any sort of conversational thread of her own of that sort. We just kept grinding to a halt, which then forced us to fish for random ideas to keep the dialogue going. It wasn't working at all...

Even though I sensed that this was going to be our last outing together fairly early on into the date, I still put on my best smile and tried to be as charming and witty as possible – just as I would on any other date. The goal was to make sure she had a pleasant experience, regardless of the possibility of a fourth date or not.

This is one of the main things that a rebbe of mine from my yeshiva in Israel stresses in his dating shiurim: the need to ensure that the girl has a good time, no matter what result comes from the date itself. This means that despite what your feelings are, or what number date it is, the guy is obligated to do his very best to make sure the girl enjoys herself and will walk away from the date with a positive impression of both the guy and dating in general.

I think people tend to get jaded with the whole shidduch process because they end up going on bad dates with people who misbehave; either in personal manners, or how they treat the person they’re with, or even their emotional expression (such as allowing facial contortions that clearly demonstrate that they’re bored or don’t like their date). If people (men and women) had a positive experience every time they went out, even if the date(s) end up being unproductive in the long run, I think their feelings of dissatisfaction with their dating lives would be somewhat lessened.

True, this doesn’t eliminate the repetitive, “here we go again” feeling that accompanies going on date after date with no result, but at least the dates themselves will be enjoyable. Also, you will have met another quality person out there in this sometimes (or is that always?) crazy dating world out there. Perhaps you’ll end up thinking about them as a potential match for a friend of yours, and your suggestion will lead to a happily married couple. As idealistic as that sounds, it does happen. Also, you would be far less likely to recommend a former date to a friend if the reason you ended things was due to how much they mistreated you or acted ungentlemanly/unladylike.

I think that one of the reasons why I’ve never had a bad date (and thus have no fun stories worth telling) is because I’ve done my best to take this lesson to heart. I often read/hear stories of guys being obnoxious on dates, and thereby making the girl suffer because of their uncouth behavior. I think that this idea that my rebbe presented should be stressed ad nauseum until every guy makes this a permanent part of their dating mindset. It really is that important.

This doesn’t preclude the idea of overly demanding, JAP-y female types causing problems, since I’ve heard about them as well. In stark contrast, the couple of girls who handed me a rejection when I was completely convinced there was going to be another date successfully acted on this notion. I had no clue what was coming, which did make the emotional impact a little more hurtful, but that early dismissal became the only negative thing I could remember about my time spent going out with them. I think that is a significant achievement.

I hope everyone who reads this will take the notion to heart – always be on your best behavior, smile, and turn on the charm, no matter what you’re thinking. The other person, who is an emotional, feeling human being (not to mention the fact that they had the decency to go out with you in the first place) deserves to have a pleasant date. If more and more people act on this principle, perhaps we can reduce the often overbearing frustration (even if ever-so-slightly) that so many people feel on their journey to find their spouse.